No-nonsense department store shopping begins at State Street, where famous Chicago retailers Marshall Field's (111 N State St) and Carson Pirie Scott (1 S State St) maintain architecturally significant HQs.

Nearly every important name brand has a flagship store along the Magnificent Mile. Start where Michigan Ave meets the Chicago River and make your way north, past block after block of non-stop shops, including American Girl Place (111 E Chicago), where thousands of girls converge daily for historically inspired dolls, and sportswear Mecca Niketown. At the end of the Magnificent Mile, just before the shop-lined street dead ends into Lake Michigan, you'll find Oak Street, home to some of the city's most exclusive boutiques, like couture-heavy Ultimo (114 E Oak St), luxury linen outposts Pratesi (67 E Oak St) and Frette (41 E Oak St), and Kate Spade handbags and accessories (101 E Oak St).

Art lovers will appreciate the city's gallery district in the River North neighbourhood. Find blueprints from Illinois native Frank Lloyd Wright at Architech (730 N Franklin St.) or American contemporary artists at Mary Bell Galleries (740 N Franklin). Lincoln Park is the destination for hip, charming boutiques like Shopgirl (1206 Webster Ave), Isabella Fine Lingerie (1101 W Webster Ave) and the Chopping Block gourmet shop (1324 W Webster Ave). Find an edgier look in Bucktown, where travelling any direction from its hub, a bustling intersection called The Six Points, yields funky footwear from John Fluevog, (1539 N Milwaukee) styles from up-and-coming designers at P.45 (1643 N Damen Ave) and exquisite flowers and gifts from Asrai Garden (1935 W North Ave).